115-20-8

Usage

Chemical Description

Trichloroethanol is a colorless liquid with a chloroform-like odor, while triethyl orthoformate is a clear, colorless liquid with a pungent odor.

Uses

Used in Pharmaceutical Industry:
Trichloroethanol is used as an intermediate for the production of various pharmaceutical compounds. It serves as a key component in the synthesis of anesthetic agents, contributing to their sedative and hypnotic effects.
Used in Chemical Synthesis:
In the field of chemical synthesis, Trichloroethanol is utilized as a protecting group for acids, acetals, and phosphoryl groups of nucleotides. Its protective function can be easily removed by zinc reduction, making it a valuable tool in the synthesis of complex molecules.
Used in Organic Chemistry:
Trichloroethanol is used in the conversion of per-O-acetylated sugars to per-O-acetylated trichloroethyl derivatives, which are important intermediates in the synthesis of various organic compounds.
Used in Acid Derivatives:
The 2,2,2-Trichloroethyl (TCE) moiety of Trichloroethanol is employed in the preparation of TCE ester of chlorosulfuric acid, which is an essential compound in the production of various acid derivatives.
Used in Biochemistry:
Trichloroethanol is used in the preparation of 2,2,2-trichloroethyl acetimidate hydrochloride, a compound that finds applications in biochemistry and molecular biology, particularly in the synthesis of nucleic acids and their analogs.

Safety Profile

Poison by intravenous andintraperitoneal routes. Moderately toxic by ingestion andrectal routes. Human mutation data reported. Explosivereaction with concentrated sodium hydroxide solutions.When heated to decomposition it emits toxic fumes ofClí. Us

InChI:InChI=1/C2H3Cl3O/c3-1-2(4,5)6/h6H,1H2

Upstream product

• 302-17-0 chloral hydrate 
• 64-17-5 ethanol 
• 515-84-4 Ethyl trichloroacetate 
• 60-29-7 diethyl ether 
• 3761-92-0 n-hexylmagnesium bromide 
• 75-87-6 chloral 
• 1462-75-5 3-phenylpropylmagnesium bromide 
• 97-93-8 triethylaluminum 
• 693-25-4 n-pentylmagnesium bromide 
• 555-75-9 aluminum ethoxide 
• 109-88-6 magnesium methanolate 
• 925-90-6 ethylmagnesium bromide 
• 557-20-0 diethylzinc 
• 555-31-7 aluminum isopropoxide 

Downstream Products

• 6270-21-9 fumaric acid bis-(2,2,2-trichloro-ethyl ester) 
• 107-69-7 Voluntal 
• 42334-34-9 2,2,2-trichloroethyl-3-methylbut-2-enoate 
• 50601-47-3 methacrylate de trichloro-2,2,2 ethyle 
• 6093-25-0 3,5-dinitro-benzoic acid-(2,2,2-trichloro-ethyl ester) 
• 60010-51-7 β,β,β-trichloroethyl phosphorodichloridite 
• 18868-46-7 2,2,2-trichloroethyl phosphorodichloridate 
• 36884-93-2 Bis-(2,2,2-trichlorethyl)-sulfit 
• 20405-30-5 tris(2,2,2-trichloroethyl) phosphate 
• 75-80-9 2,2,2-tribromoethanol 
• 97631-94-2 2-chloro-benzoic acid-(2,2,2-trichloro-ethyl ester) 
• 37934-99-9 2,2,2-trichloroethyl benzoate 
• 97631-97-5 4-chloro-benzoic acid-(2,2,2-trichloro-ethyl ester) 
• 126336-29-6 4-methoxy-benzoic acid-(2,2,2-trichloro-ethyl ester) 

Related news

Short communicationInhibition by chloral hydrate and Trichloroethanol (cas 115-20-8) of AMPA-induced Ca2+ influx in rat cultured cortical neurones08/31/2019

The effects of chloral hydrate and its main metabolite 2,2,2-trichloroethanol were investigated on the (S)-α-amino-3-hydroxy-5-methyl-4-isoxazolepropionate (AMPA)-induced rise of intracellular Ca2+ concentration ([Ca2+]i) in cultured non-pyramidal cortical neurones of rats by using single-cell ...detailed

Trichloroethanol (cas 115-20-8) up-regulates matrix metalloproteinase-9 and tissue inhibitor of metalloproteinase-1 in HaCaT cells08/27/2019

Occupational trichloroethylene (TCE) exposure could induce generalized skin hypersensitivity reactions complicated with severe liver dysfunctions. Active extracellular matrix degradation and remodeling are involved in the skin hypersensitivity reaction induced by chemical exposure. In the presen...detailed

Trichloroethanol (cas 115-20-8) enhances the activity of recombinant human TREK-1 and TRAAK channels08/26/2019

Human TREK-1 and TRAAK (hTREK-1 and hTRAAK) are the recently cloned tandem pore-domain potassium channels that are highly expressed in the central nervous system (CNS). The roles of 2P domain K+ channels in general anesthesia and neuroprotection have been proposed recently. We have investigated ...detailed

Trichloroethylene oxidative metabolism in plants: the Trichloroethanol (cas 115-20-8) pathway08/22/2019

Trichloroethylene (TCE) is a widespread and persistent environmental contaminant. Recently, plants, poplar trees in particular, have been investigated as a tool to remove TCE from soil and groundwater. The metabolism of TCE in plants is being investigated for two reasons: one, plant uptake and m...detailed

Relevant academic research and scientific papers

Degradation pathways of trichloroethylene and 1,1,1-trichloroethane by Mycobacterium sp. TA27

We analyzed the kinetics and metabolic pathways of trichloroethylene and 1,1,1-trichloroethane degradation by the ethane-utilizing Mycobacterium sp. TA27. The apparent Vmax and Km of trichloroethylene were 9.8 nmol min-1 m

Laser Photolysis/Laser-Induced Fluorescence Studies of the Reaction of OH with 1,1,1-Trichloroethane over an Extended Temperature Range

Absolute rate coefficients are determined for the gas-phase reaction of OH radicals with 1,1,1-trichloroethane over an extended temperature range.Employing a laser photolysis/laser-induced fluorescence technique, experiments were conducted with a flow system at a total pressure of 740 +/- 10 Torr using He as diluent and carrier gas.The rate coefficients, obtained over the temperature range 298-761 K, exhibited pronounced non-Arrhenius behavior and were best described by the modified Arrhenius equation k(T)=(3.95 +/- 0.78) x 10-13(T/300)2.08exp cm3 molecule-1 s-1.Comparison of the data with numerous lower temperature measurements is presented.The temperature dependence of the data is compared with empirical and transition-state model calculations.The reactivity of this compound with OH compared to other chlorinated ethanes at both lower and higher reaction temperatures is presented and discussed.

Laser Photolysis/Laser-Induced Fluorescence Studies of the Reaction of OH with 1,1-Dichloroethane over an Extended Temperature Range

Absolute rate coefficients are determined for the gas-phase reaction of OH radicals with 1,1-dichloroethane over an extended temperature range using a laser photolysis/laser-induced fluorescence technique.Experiments were performed in a flow system at a total pressure of 740 +/- 10 Torr using He as diluent and carrier gas.The rate coefficients, obtained over the temperature range 294-800 K, exhibited pronounced non-Arrhenius behavior and were best described by the modified Arrhenius equation k(T)=(8.29 +/- 0.36) x 10-14(T/300)2.67exp cm3 molecule-1 s-1.Comparison of the data with one previous room-temperature measurement is presented.The temperature dependence of the data is compared with empirical and transition-state model calculations.The influence of C-H bond energy and Cl substitution is discussed.

Kinetics of the Reactions of OH with C2H6, CH3CCl3, CH2ClCHCl2, CH2ClCClF2, and CH2FCF3

The rate constants of the five H-abstraction reactions are measured from about 250 to 470 K by using the discharge-flow technique.Arrhenius parameters, three-parameter fits, and modified A and E values centered at 300 K are obtained.As in earlier papers on substituted methanes, Ath300 is calculated by thermochemical transition-state theory and compared with Aexp300, giving good agreement, on average, for a C-H-O bond angle of 150 deg.Three-parameter fits are reexamined for the ten methane reactions, their usefulness is discussed, and the dependence of Aexp300 on n, the temperature exponent, is calculated.Consequently, it is suggested that fitting routines be guided by theoretical considerations.

High utility of Saccharomyces cerevisiae harboring rat liver cytochrome P450 1A2 cDNA in haloethanes dehalogenations

Yeast harboring rat liver P450 1A2 efficiently degraded trichloroethylene, pentachloroethane and hexachloroethane. Since liver P450s catalyze degradation of thousands of chemicals, this method is promising for chemical-directed degradation of environmental pollutants.

Microwave-assisted Cannizzaro reaction—Optimisation of reaction conditions

The microwave-assisted Cannizzaro reaction was studied in order to develop fully reproducible synthetic protocols for transformation of aldehydes to carboxylic acid and alcohols. Optimised were the following process parameters: power, temperature, and time. Aromatic, heteroaromatic and aliphatic aldehydes were used in the studies. It was found that furfural, thiophene-2-carbaldehyde, pyridinecarboxaldehyde and aromatic aldehydes react under mild conditions, while 1-methyl-pyrrole-2-carboxaldehyde derivatives and aliphatic aldehydes require more drastic reaction conditions and a longer exposure time to microwave radiation.

A DMAP-catalyzed approach to the industrial-scale preparation of N -6-demethylated 9,10-dihydrolysergic acid methyl ester: A key cabergoline and pergolide precursor

A scalable new approach for the preparation of N-6-demethylated 9,10-dihydrolysergic acid methyl ester using 2,2,2-trichloroethyl chloroformate was developed. A key discovery that enabled the efficient and industrial-scalable process is linked to the rigorous extrusion of water in the reaction system and application of an organic catalyst such as 4-(N,N-dimethylamino)pyridine (DMAP) instead of the alkali metal bicarbonate additives. Namely, in the previously known process, the concomitant presence of bicarbonates and traces of water triggers side reaction cycles that produce and accumulate hydrochloric acid and water. The former slows down the reaction. Moreover, these cycles cause the formation of multiple carbonate and alcohol-type side products to a significant extent that provide a low-quality N-6-demethylated product. All of these shortcomings are circumvented by the application of DMAP as a catalyst and the use of a reaction medium free of water. This approach allows operation on an industrial scale (51 kg batch) with higher yields, shorter reaction times, and improved product quality.

Introducing a mixed-valent dirhodium(ii,iii) catalyst with increased stability in C-H amination

A new mixed-valent Rh2II,III dimer, [Rh 2(espn)2Cl] (espn2- = α,α, α′,α′-tetramethyl-1,3-benzenedipropanamidate), is reported. This compound readily dissociates Cl- at low concentrations in solution to form the active [Rh2(espn)2]+ catalyst, which performs intramolecular C-H amination with TONs > 1400. This work expands the scope of Rh2II,III dimers to nitrenoid chemistry.

Practical and chemoselective reduction of acyl chloride to alcohol by borohydride in aqueous dichloromethane

A simple methodology for the reduction of acid chlorides to their corresponding alcohols has been developed. Various carboxylic acids were converted to alcohols in excellent yields using NaBH4-K2CO3 in a mixed solvent system of dichloromethane and water (1:1) in the presence of a phase-transfer catalyst at low temperature. The importance of the work is its simplicity, selectivity, excellent yield, and very short reaction time. This new reduction condition has proved to be an excellent chemoselective method for a range of acid chlorides in the presence of various functional groups.

1,2-H shift in copper-chlorocarbenoid intermediate during CuCl/bpy-promoted stereoselective dechlorination of 2,2,2-trichloroethyl alkyl ethers to (Z)-1-alkoxy-2-chloroethenes

(Chemical Equation Presented) Reaction of 2,2,2-trichloroethyl alkyl ethers with 2 molar equiv of CuCl/bpy in refluxing DCE yielded (Z)-1-alkoxy-2- chloroethenes stereoselectively as the major product via 1,2-H shift in copper-chlorocarbenoid intermediate. 2,2,2-Trichloroethyl carboxylates undergo a radical 1,2-acyloxy shift under similar conditions.